Synergistic effects of alkanolamine alkylamides and other moisturizing agents

ABSTRACT

The disclosure provides personal care compositions that comprise a moisturizing agent of formula (I) wherein n is an integer from 2 to 5, R 1  is independently H or C 1 -C 3  alkyl and R 2  is an unsubstituted linear or branched C 1 -C 6  alkyl, at least one additional moisturizing agent and a cosmetically acceptable vehicle. In particular, the compound of formula (I) is diglycolamine acetamide. The compositions generally improve moisturization of skin and hair.

BACKGROUND OF THE INVENTION Field of the Invention

The disclosure generally provides personal care formulations that improve moisturization.

Description of Related Art

A significant segment of the population uses products to moisturize their skin and/or hair, and such segment continues to grow at a substantial rate. When trying to provide or increase moisturizing efficacy, many of the moisturizing products currently on the market also leave a heavy, greasy feel that consumers find undesirable. Thus there is a need in the art for a long-lasting moisturizer that does not have qualities undesirable to the user.

SUMMARY OF THE INVENTION

We recognized a need for personal care formulations with improved moisturizing efficacy. Several humectants have been known and used in personal care formulation. Many of the known humectants, including the most widely used (glycerol), are sticky, tacky, or greasy when applied on the skin. In a broad aspect, the disclosure provides personal care formulations that have an improved, smooth feel on the skin that is desirable by the consumers. Specifically, the personal care formulations of the disclosure exhibit less greasiness, stickiness, tackiness, or heavy feeling, and, for example, are easy to spread on the skin. Furthermore, the personal care formulations of the disclosure have improved moisturization efficacy on skin and/or hair.

Thus, one aspect of the disclosure provides personal care formulations comprising

-   -   (a) a first moisturizing agent comprising a compound of formula         (I)

-   -   -   wherein         -   n is an integer from 2 to 5;         -   R¹ is independently H or C₁-C₃ alkyl; and         -   R² is an unsubstituted linear or branched C₁-C₆ alkyl;

    -   (b) at least one additional moisturizing agent;

    -   and

    -   (c) a cosmetically acceptable vehicle.

In another aspect, the disclosure provides personal care formulations comprising (a) a moisturizing agent comprising a compound of formula (I); (b) at least one additional moisturizing agent; and (c) a cosmetically acceptable vehicle, wherein the combination of component (a) and component (b) provides an increase in moisturization greater than either component (a) or component (b) alone, on a corresponding weight basis, such that the combination of component (a) and component (b) produces a synergistic relative moisturization efficacy. In some embodiments, the personal care formulations of the disclosure also can provide long term moisturization, for example, up to 30 hours after a single application.

In another aspect, the disclosure provides a kit comprising a container (e.g., a tube or jar) containing a personal care formulation according to the disclosure and instructions for application of the formulation to the skin or hair for enhancing moisturization of the skin or hair, wherein the instructions are printed on the container, on the packaging of the container, or on a document included with the container as part of the kit.

In another aspect, the disclosure provides a method of moisturizing skin or hair, the method comprising applying an effective moisturizing amount of a personal care formulation of the disclosure to the skin or hair, respectively.

In another aspect, the disclosure provides for the use of a moisturizing agent comprising a compound of formula (I) above and at least one additional moisturizing agent as a humectant composition in a personal care formulation.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 shows Dynamic Vapor Sorption values for compositions of various moisturizing agents, both singly and in combination, as described in Example 3.

FIG. 2 provides Corneometer values of glycerol and water treatment for 8 panelists after 6 hours of treatments, as described in Example 4.

FIG. 3 provides Corneometer values of diglycolamine (DGA) Acetamide for 8 panelists after 6 hours of treatments, as described in Example 4.

FIG. 4 provides scaled moisturization performance of DGA Acetamide for 8 panelists after 6 hours of treatments by adjusting humectance value of water to 0 and humectance value of glycerol to 1, as described in Example 4.

FIG. 5 shows scaled moisturization performance (SMP) measured after six hours for compositions of various moisturizing agents, both singly and in combination.

FIG. 6 shows scaled moisturization performance (SMP) measured after 30 hours for compositions of various moisturizing agents, both singly and in combination.

DETAILED DESCRIPTION OF THE INVENTION

Before the disclosed materials and methods are described, it is to be understood that the aspects described herein are not limited to specific embodiments, or configurations, and as such can, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and, unless specifically defined herein, is not intended to be limiting.

In view of the present disclosure, the active materials and methods described herein can be configured by the person of ordinary skill in the art to meet the desired need. In general, the disclosed materials provide improvements in personal care formulations, particularly in the skin care and hair care formulations. For example, in certain aspects, the personal care formulations of the disclosure have improved moisturization efficacy on skin and/or hair. In addition, in some embodiments the personal care compositions of the disclosure can provide long term moisturization; for example, up to 30 hours after a single application.

Several humectants have been known and used in personal care formulations. The most widely used humectant, glycerol, is sticky, and greasy when applied on the skin. In contrast, the personal care formulations of the disclosure have improved feel on the skin. Specifically, the disclosed compositions exhibit less greasiness, stickiness, tackiness, or heavy feeling, and are easy to spread on the skin.

Personal care formulations of the disclosure comprise

-   -   (a) a first moisturizing agent comprising a compound of formula         (I)

-   -   wherein     -   n is an integer from 2 to 5;     -   R¹ is independently H or C₁-C₃ alkyl; and     -   R² is an unsubstituted linear or branched C₁-C₆ alkyl, and     -   (b) at least one additional moisturizing agent, and     -   (c) a cosmetically acceptable vehicle.

In certain embodiments of the compound of formula (I), n is an integer from 2 to 4. In other embodiments of the compound of formula (I), n is selected from 2 or 3. In one embodiment of the compound of formula (I), n is 2. In another embodiment of the compound of formula (I), n is 3.

In one embodiment of the compound of formula (I), R¹ is independently selected from H, methyl, and ethyl. In another embodiment, R¹ is independently selected from H and methyl. In certain embodiments, R¹ is independently H. In other certain embodiments, R¹ is independently methyl.

In certain embodiments of the compound of formula (I) according to any preceding embodiment, R² is unsubstituted linear or branched C₁-C₄ alkyl. In one embodiment, R² is selected from methyl and ethyl. In another embodiment, R² is methyl.

An example of a particularly useful compound of formula (I) is:

also referred to as N-acetyl diglycolamine, N-acetyl DGA, diglycolamine acetamide or DGA Acetamide.

One known method for preparing DGA Acetamide is reported in Krakowiak et al., “A New Building Block Method To Synthesize Symmetrical and Asymmetrical Per-N-alkyl-Substituted Polyaza-Crown Compounds,” J. Org. Chem., 54(17): 4061-4067 (1989).

The compound of formula (I) acts as a humectant capable of providing moisturization by, for example, retaining water. Thus, in some embodiments, the compound (I) is present in component (a) in an amount sufficient to provide an increase in moisturization of skin or hair with which it comes into contact.

In certain embodiments, the compound of formula (I) is present in about 0.5% to about 15% by weight of the personal care formulation. In other embodiments, the compound of formula (I) is present in about 0.5 wt % to about 14 wt %, or about 0.5 wt % to about 13 wt %, or about 0.5 wt % to about 12 wt %, or about 0.5 wt % to about 11 wt %, or about 0.5 wt % to about 10 wt %, or about 0.5 wt % to about 9 wt %, or about 0.5 wt % to about 8 wt %, or about 0.5 wt % to about 7 wt %, or about 0.5 wt % to about 6 wt %, or about 1 wt % to about 15 wt %, about 1 wt % to about 14 wt %, or about 1 wt % to about 13 wt %, or about 1 wt % to about 12 wt %, or about 1 wt % to about 11 wt %, or about 1 wt % to about 10 wt %, or about 1 wt % to about 9 wt %, or about 1 wt % to about 8 wt %, or about 1 wt % to about 7 wt %, or about 1 wt % to about 6 wt %, or about 2 wt % to about 15 wt %, about 2 wt % to about 14 wt %, or about 2 wt % to about 13 wt %, or about 2 wt % to about 12 wt %, or about 2 wt % to about 11 wt %, or about 2 wt % to about 10 wt %, or about 2 wt % to about 9 wt %, or about 2 wt % to about 8 wt %, or about 2 wt % to about 7 wt %, or about 2 wt % to about 6 wt %, or about 2 wt % to about 5 wt %, or about 3 wt % to about 15 wt %, about 3 wt % to about 14 wt %, or about 3 wt % to about 13 wt %, or about 3 wt % to about 12 wt %, or about 3 wt % to about 11 wt %, or about 3 wt % to about 10 wt %, or about 3 wt % to about 9 wt %, or about 3 wt % to about 8 wt %, or about 3 wt % to about 7 wt %, or about 3 wt % to about 6 wt %, or about 3 wt % to about 5 wt %, or about 4 wt % to about 15 wt %, about 4 wt % to about 14 wt %, or about 4 wt % to about 13 wt %, or about 4 wt % to about 12 wt %, or about 4 wt % to about 11 wt %, or about 4 wt % to about 10 wt %, or about 4 wt % to about 9 wt %, or about 4 wt % to about 8 wt %, or about 4 wt % to about 7 wt %, or about 4 wt % to about 6 wt %, or about 4 wt % to about 5 wt %, or about 4.5 wt % to about 6.5 wt %, about 4.5 wt % to about 6 wt %, or about 4.5 wt % to about 5.5 wt %, or about 5 wt % to about 15 wt %, about 5 wt % to about 14 wt %, or about 5 wt % to about 13 wt %, or about 5 wt % to about 12 wt %, or about 5 wt % to about 11 wt %, or about 5 wt % to about 10 wt %, or about 5 wt % to about 9 wt %, or about 5 wt % to about 8 wt %, or about 5 wt % to about 7 wt %, or about 5 wt % to about 6 wt %, or about 4.5 wt % to about 5 wt %, or about 4.5 wt %, or about 5 wt %, or about 5.5 wt %, or about 6 wt %, of the personal care formulation. In certain embodiments, the compound of formula (I) is present in about 1% to about 4% by weight of the personal care formulation. In some other embodiments, the compound of formula (I) is present in about 1.5% to about 3.5% by weight of the personal care formulation. In some other embodiments, the compound of formula (I) is present in about 0.5% to about 2.5% by weight of the personal care formulation. In some other embodiments, the compound of formula (I) is present in about 5 to about 10% by weight of the personal care formulation.

The personal care formulations of the disclosure also include at least one additional moisturizing agent as component (b). Such additional moisturizing agents are known in the art and include without limitation occlusion compounds such as petrolatum, mineral oils, vegetable oils, triglycerides, lanolins and their derivatives, unsaturated fatty acids and their derivatives, silicones, and some emollients; humectants such as glycerol, sorbitol, lactates (including, but not limited to sodium, ammonium, and potassium salts), hydroxyalkyl ureas, polyols (e.g., propylene glycol), polyethylene glycol (PEG 200-600), and Sorbeth-30; natural moisturizing factors (NMFs) such as urea, lactic acid, and sodium pyrrolidone carboxylic acid (NaPCA); liposomes, natural and vegetal moisturizing agents such as serine, chitosan PCA, sodium hyaluronate, hyaluronic acid, microsponges, soluble collagen, modified protein, sugars, monosodium L-glutamate, lecithins and phospholipids and their derivatives; α- and β-hydroxy acids such as glycolic acid, lactic acid, citric acid, maleic acid and salicylic acid; polymeric moisturizers such as polysaccharides and their derivatives such as modified starch, xanthan gum and dehydroxanthan gum, polyacrylates, and polyquaternium-4, -10 and -51; and amino acids such as glutamic acid, aspartic acid, and lysine.

As used herein, all acids are intended to include the salts thereof.

Particularly suitable additional moisturizing agents of component (b) include petrolatum, mineral and vegetable oils, lanolins, glycerol, sorbitol, polyols, urea, hydroxyalkylurea, lactic acid, lactates, sugars, alpha hydroxy acids, beta hydroxy acids, sodium hyaluronate, hyaluronic acid, pyrrolidone carboxylic acid, and pyrrolidone carboxylates, and combinations thereof. In one embodiment the at least one additional moisturizing agent is selected from one or more of the group consisting of glycerol, polyols, hydroxyalkyl ureas, pyrrolidone carboxylic acids and salts thereof, lactic acids and salts thereof, and combinations thereof. In one embodiment the at least one additional moisturizing agent is selected from glycerol, hydroxyethyl urea, sodium lactate, sodium pyrrolidone carboxylate, and combinations thereof. In one embodiment, the personal care formulations of the disclosure include only one additional moisturizing agent selected from the group consisting of glycerol, hydroxyethyl urea, sodium lactate, and sodium pyrrolidone carboxylate. In another embodiment, the personal care formulations of the disclosure include two or more additional moisturizing agents selected from the group consisting of glycerol, hydroxyethyl urea, sodium lactate, and sodium pyrrolidone carboxylate. In one embodiment, the personal care formulations of the disclosure include one additional moisturizing agent that is glycerol. In another embodiment, the personal care formulations of the disclosure include one additional moisturizing agent that is hydroxyethyl urea. In another embodiment, the personal care formulations of the disclosure include one additional moisturizing agent that is sodium lactate. In another embodiment, the personal care formulations of the disclosure include one additional moisturizing agent that is sodium pyrrolidone carboxylate. In one embodiment, the personal care formulations of the disclosure include one additional moisturizing agent that is glycerol, and at least one further additional moisturizing agent selected from the group consisting of hydroxyethyl urea, sodium lactate, and sodium pyrrolidone carboxylate. In one embodiment the personal care formulations of the invention include one additional moisturizing agent that is glycerol and one additional moisturizing agent that is hydroxyethyl urea. In one embodiment, the personal care formulations of the disclosure include at least one additional moisturizing agent selected from glycerol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,2-pentanediol, 1,5-pentanediol, 1,2-hexanediol, 1,6-hexanediol, 1,2-octanediol, butane-1,2,3,4-tetraol, pentane-1,2,3,4,5-pentaol, hexane-1,2,3,4,5,6-hexol, erythritol, xylitol, sorbitol, glucose, maltose, lactose, lactitol, sucrose, and maltodextrin.

In certain embodiments, the at least one additional moisturizing agent of component (b) is present in about 0.5% to about 15% by weight of the personal care formulation. In other embodiments, the at least one additional moisturizing agent is present in about 0.5 wt % to about 14 wt %, or about 0.5 wt % to about 13 wt %, or about 0.5 wt % to about 12 wt %, or about 0.5 wt % to about 11 wt %, or about 0.5 wt % to about 10 wt %, or about 0.5 wt % to about 9 wt %, or about 0.5 wt % to about 8 wt %, or about 0.5 wt % to about 7 wt %, or about 0.5 wt % to about 6 wt %, or about 1 wt % to about 15 wt %, about 1 wt % to about 14 wt %, or about 1 wt % to about 13 wt %, or about 1 wt % to about 12 wt %, or about 1 wt % to about 11 wt %, or about 1 wt % to about 10 wt %, or about 1 wt % to about 9 wt %, or about 1 wt % to about 8 wt %, or about 1 wt % to about 7 wt %, or about 1 wt % to about 6 wt %, or about 2 wt % to about 15 wt %, about 2 wt % to about 14 wt %, or about 2 wt % to about 13 wt %, or about 2 wt % to about 12 wt %, or about 2 wt % to about 11 wt %, or about 2 wt % to about 10 wt %, or about 2 wt % to about 9 wt %, or about 2 wt % to about 8 wt %, or about 2 wt % to about 7 wt %, or about 2 wt % to about 6 wt %, or about 2 wt % to about 5 wt %, or about 3 wt % to about 15 wt %, about 3 wt % to about 14 wt %, or about 3 wt % to about 13 wt %, or about 3 wt % to about 12 wt %, or about 3 wt % to about 11 wt %, or about 3 wt % to about 10 wt %, or about 3 wt % to about 9 wt %, or about 3 wt % to about 8 wt %, or about 3 wt % to about 7 wt %, or about 3 wt % to about 6 wt %, or about 3 wt % to about 5 wt %, or about 4 wt % to about 15 wt %, about 4 wt % to about 14 wt %, or about 4 wt % to about 13 wt %, or about 4 wt % to about 12 wt %, or about 4 wt % to about 11 wt %, or about 4 wt % to about 10 wt % or about 4 wt % to about 9 wt %, or about 4 wt % to about 8 wt %, or about 4 wt % to about 7 wt %, or about 4 wt % to about 6 wt %, or about 4 wt % to about 5 wt %, or about 4.5 wt % to about 6.5 wt %, or about 4.5 wt % to about 6 wt %, or about 5 wt % to about 15 wt %, about 5 wt % to about 14 wt %, or about 5 wt % to about 13 wt %, or about 5 wt % to about 12 wt %, or about 5 wt % to about 10 wt %, or about 5 wt % to about 9 wt %, or about 5 wt % to about 8 wt %, or about 5 wt % to about 7 wt %, or about 5 wt % to about 6 wt %, or about 4.5 wt % to about 5.5 wt %, or about 4.5 wt % to about 5 wt %, or about 4.5 wt %, or about 5 wt %, or about 5.5 wt %, or about 6 wt %, of the personal care formulation. In certain embodiments, the at least one additional moisturizing agent is present in about 1% to about 4% by weight of the personal care formulation. In some other embodiments, the at least one additional moisturizing agent is present in about 1.5% to about 3.5% by weight of the personal care formulation. In some other embodiments, the at least one additional moisturizing agent is present in about 0.5% to about 3.5% by weight of the personal care formulation. In some other embodiments, the compound of formula (I) is present in about 5 to about 10 % by weight of the personal care formulation.

When provided together in a personal care formulation, the compound of formula (I) of component (a) and the at least one additional moisturizing agent of component (b) are present in a synergistically moisturizing effective ratio by weight. In one embodiment, the weight ratio of the compound of formula (I) of component (a) to the at least one additional moisturizing agent of component (b) is at least about 0.5:15 and no more than about 15:0.05. In another embodiment, the synergistically moisturizing effective weight ratio of the compound of formula (I) to the at least one additional moisturizing agent is from about 1:10 to about 10:1.In another embodiment, the synergistically moisturizing effective weight ratio of the compound of formula (I) to the at least one additional moisturizing agent is from about 1:5 to about 5:1. In another embodiment, the synergistically moisturizing effective weight ratio is from about 1:4 to about 4:1, or from about 1:3 to about 3:1, or from about 1:2 to about 2:1, or from about 1:1 to about 2:1, or from about 1:2 to about 1:1, or about 1:1, or about 2:1, or about 3:1, or about 4:1, or about 5:1, or about 1:2, or about 1:3, or about 1:4, or about 1:5. In one embodiment, the synergistically moisturizing effective weight ratio of the compound of formula (I) to the at least one additional moisturizing agent is 1:1. In another embodiment, the synergistically moisturizing effective ratio of the compound of formula (I) to the at least one additional moisturizing agent is about 3:5, or about 3:4, or about 1:1.2 to about 1:1.3 by weight.

The personal care formulations of the disclosure also include a cosmetically acceptable vehicle as component (c). While the vehicle for personal care formulations can comprise a relatively simple solvent or dispersant such as water, such vehicles can also vary greatly depending upon the type of formulation (e.g., skin care or hair care) and the functionality and properties desired. For example, the cosmetically acceptable vehicle may be selected to be more conducive to topical application, including one that will form a film or layer on the skin to which the formulation is applied so as to localize the application and provide some resistance to washing off by immersion in water or by perspiration. The vehicles can be creams, lotions, gels, serums, emulsions, or other liquids and can include additional ingredients such as thickening agents (such as gums) or hydrophilic colloids. The cosmetically acceptable vehicle may comprise an aqueous phase, an oil phase, an alcohol, a silicone phase or mixtures thereof. The cosmetically acceptable vehicle may also comprise an emulsion. Non-limiting examples of suitable emulsions include water-in-oil emulsions, oil-in-water emulsions, silicone-in-water emulsions, water-in-silicone emulsions, wax-in-water emulsions, water-oil-water triple emulsions or the like having the appearance of a cream, gel or microemulsions. The emulsion may include an emulsifier, such as a nonionic, anionic or amphoteric surfactant. Suitable cosmetically acceptable vehicles and other components are well known to those skilled in the cosmetic formulation art and can be found, for example in McCutcheon's 2015 Emulsifiers and Detergents: North American Edition by Michael Allured, MC Publishing Co., 2015 edition (Mar. 2, 2015), and in McCutcheon's 2015 Functional Materials: North American Edition by Michael Allured, MC Publishing Co., 2015 edition (Mar. 2, 2015), both of which are incorporated by reference herein.

Without limitation, the personal care formulations may comprise one or more of thickeners, surfactants, emulsifiers, suspending agents, pH adjusters and neutralizers (such as lactic acid, citric acid, and the like), humectants, moisturizers, emollients, oils, waxes, solvents, chelating agents, silicones, neutralizing agents, preservatives, fragrances, dyes, pigments, conditioners, polymers, exfoliants, film formers, propellants, hair fixatives and colorants, and any combination thereof. The compound of formula (I) of the present disclosure is compatible with most other components used in conventional personal care formulations. For example, cosmetic formulations may also contain one or more other components such as vitamins, antioxidants, botanical extracts, styling agents, antiperspirant active ingredients, anti-acne agents, anti-dandruff actives, UV filters, sunscreen actives, tanning accelerators, and other active ingredients.

The CTFA Cosmetic Ingredient Handbook, Seventh Edition, 1997 and the Eighth Edition, 2000, which is incorporated by reference herein in their entirety, describe a wide variety of cosmetic and pharmaceutical ingredients commonly used in skin care compositions that are suitable for use in the compositions of the present disclosure. Examples of these functional classes disclosed in this reference include: absorbents, abrasives, anticaking agents, antifoaming agents, antioxidants, binders, biological additives, buffering agents, bulking agents, chelating agents, chemical additives, colorants, cosmetic astringents, cosmetic biocides, denaturants, depilatory compounds, drug astringents, external analgesics, film formers, fragrance components, opacifying agents, pH adjusters (such as lactic acid, citric acid, and the like), plasticizers, reducing agents, skin bleaching agents, skin-conditioning agents (emollient, humectants, miscellaneous, and occlusive), skin protectants, solvents, foam boosters, hydrotropes, solubilizing agents, suspending agents (nonsurfactant), sunscreen agents, ultraviolet light absorbers, SPF boosters, insect repellants, waterproofing agents, and viscosity increasing agents (aqueous and nonaqueous).

The personal care formulations of the disclosure may include one or more thickening agents. The formulations of the present invention may comprise from about 0.01% to about 10% by weight, from about 0.05% to about 1% by weight, from about 0.1% to about 0.5% by weight, or, alternatively, from about 0.1% to about 0.25% by weight, of a thickening agent or a mixture of thickening agents when present. Suitable classes of thickening agents include but are not limited to carboxylic acid polymers, polyacrylamide polymers, sulfonated polymers, copolymers thereof, hydrophobically modified derivatives thereof, and mixtures thereof. Suitable thickening agents include carboxylic acid polymers such as the carbomers (e.g., the CARBOPOL® 900 series such as CARBOPOL® 940, CARBOPOL® 954 and Carbopol ETD 2050), and Ultrez 10 and Ultrez 30. Other suitable carboxylic acid polymeric agents include copolymers of C10-30 alkyl acrylates with one or more monomers of acrylic acid, methacrylic acid, or one of their short chain (i.e., C1-4 alcohol) esters, wherein the crosslinking agent is an allyl ether of sucrose or pentaerytritol. These copolymers are known as acrylates/C10-30 alkyl acrylate crosspolymers and are commercially available as CARBOPOL® 1342, CARBOPOL® 1382, Ultrez 20, Ultrez 21, PEMULEN TR-1, and PEMULEN TR-2.

The personal care formulations of the disclosure may include one or more surfactants. The formulations of the present invention may comprise from about 0.01% to about 15% by weight, from about 0.05% to about 5% by weight, from about 0.05% to about 1% by weight, from about 0.1% to about 0.5% by weight, or, alternatively, from about 0.1% to about 0.25% by weight, of a surfactant or a mixture of surfactants. The exact surfactant or surfactant mixture chosen will depend upon the pH of the formulation and the other components present. Suitable surfactants include anionic, nonionic, cationic, amphoteric, or zwitterionic surfactants. The term surfactant also includes salts of fatty acids, which are typically referred to as soaps. Suitable anionic surfactants include, but are not limited to, soaps or salts of fatty acids, alkyl sulfates, alkyl ether sulfates, alpha-olefin sulfonates, alkyl aryl sulfonates, sarcosinates, alkyl glucose esters or their alkoxylates, sodium lauryl sulfate, ammonium lauryl sulfate, triethanolamine lauryl sulfate, sodium laureth sulfate, isethionates, and triethanolamine stearate. Nonionic surfactants include, but are not limited to, methyl glucose stearates or their ethoxylates, alkyl polyglucosides, and glycerol monostearate, fatty acid alkanol amides, alkyl aryl polyglycol ether, polyglycol ethers and in particular cocoyl diethanolamide, nonoxynol-7 and octoxynol-9. Exemplary cationic surfactants include, but are not limited to, mono- and di-dimethyl ammonium salts, benzalkonium chlorides, di-steary-di-methyl ammonium salts, alkyl trimethyl ammonium salts, quaternized amides of ethylene diamine, alkyl pyridinium salts, cetrimonium chloride, stearalkonium chloride and cetyl pyridinium chloride; and amphoterics including alkyl β-aminopropionates, betaines, alkyl imidazolines, cocamidopropyl betaine and caproam phocarboxy propionate.

The personal care formulations of the disclosure may include one or more emulsifiers. The formulations of the present invention may comprise from about 0.01% to about 10% by weight, from about 0.05% to about 5% by weight, from about 0.05% to about 1% by weight, from about 0.1% to about 0.5% by weight, or, alternatively, from about 0.1% to about 0.25% by weight, of an emulsifier or a mixture of emulsifiers. Exemplary emulsifiers include, but are not limited to, polyoxyethylene oleyl ether, PEG-40 stearate, ceteareth-12, Eumulgin B-1 (Henkel), ceteareth-20, Eumulgin B-2 (Henkel), ceteareth-30, Lanette (Henkel), glyceryl stearate Cutina GMS (Henkel), PEG-100 stearate, methyl myristate, isopropyl myristate, Arlacel 165, glyceryl stearate, PEG-100 stearate, steareth-2 and steareth-20, dimethicone copolyol, Polysorbate 20 (Tween 20), Polysorbate 40 (Tween 40), Polysorbate 60 (Tween 60), Polysorbate 80 (Tween 80), lauramide DEA, cocamide DEA, and cocamide MEA, Phospholipid PTC, alginate, carrageenan, Glucate DO, methylcellulose, polyvinyl alcohol, Cocamidopropyl phosphatidyl PG-dimonium chloride, stearic acid, magnesium stearate, milk amino acids, triethanolamine, and magnesium aluminum silicate.

The personal care formulations of the disclosure may also include one or more preservatives. The formulations of the present invention may comprise from about 0.01% to about 10% by weight, from about 0.05% to about 5% by weight, from about 0.05% to about 1% by weight, from about 0.1% to about 0.5% by weight, or, alternatively, from about 0.1% to about 0.25% by weight, of a preservative or a mixture of preservatives. Exemplary preservatives suitable for use in the present invention may include, but are not limited to, 5-chloro-2-methyl-1,2-thiazol-3-one, 2-methyl-1,2-thiazol-3-one, 1,3-dimethylol-5,5-dimethylhydantoin, 3-iodo-2-propynyl butyl carbamate, KATHON™ CG and GLYDANT™PLUS™, and parabens such as methylparaben and propylparaben. Additional preservatives may also be used if desired and include well known preservative compositions such as benzyl alcohol, phenyl ethyl alcohol and benzoic acid, diazolydinyl, urea, and chlorphenesin, among others.

The personal care formulations of the disclosure may also include one or more emollients. An emollient is an oleaginous or oily substance which helps to smooth and soften the skin, and may also reduce its roughness, cracking or irritation. Typical suitable emollients include mineral oil having a viscosity in the range of 50 to 500 centipoise (cps), lanolin oil, coconut oil, cocoa butter, olive oil, almond oil, macadamia nut oil, aloe extracts such as aloe vera lipoquinone, synthetic jojoba oils, natural sonora jojoba oils, safflower oil, corn oil, liquid lanolin, cottonseed oil, grape seed oil, sweet almond oil, and peanut oil. Preferably, the emollient is a cocoglyceride, which is a mixture of mono, di- and triglycerides of cocoa oil, sold under the trade name of Myritol 331 from Henkel KGaA, or Dicaprylyl Ether available under the trade name Cetiol OE from Henkel KGaA or a C12-C15 Alkyl Benzoate sold under the trade name Finsolv TN from Finetex. One or more emollients may be present ranging in amounts from about 1 percent to about 10 percent by weight, preferably about 5 percent by weight. Another suitable emollient is DC 200 Fluid 350, a silicone fluid, available Dow Corning Corp.

Other suitable emollients include squalane, castor oil, polybutene, sweet almond oil, avocado oil, calophyllum oil, ricin oil, vitamin E acetate, olive oil, silicone oils such as dimethylopolysiloxane and cyclomethicone, linolenic alcohol, oleyl alcohol, the oil of cereal germs such as the oil of wheat germ, isopropyl palmitate, octyl palmitate, isopropyl myristate, hexadecyl stearate, butyl stearate, decyl oleate, acetyl glycerides, the octanoates and benzoates of (C12-C15) alcohols, the octanoates and decanoates of alcohols and polyalcohols such as those of glycol and glyceryl, ricinoleates esters such as isopropyl adipate, hexyl laurate and octyl dodecanoate, dicaprylyl maleate, hydrogenated vegetable oil, phenyltrimethicone, jojoba oil and aloe vera extract.

Other suitable emollients which are solids or semi-solids at ambient temperatures may be used. Such solid or semi-solid cosmetic emollients include glyceryl dilaurate, hydrogenated lanolin, hydroxylated lanolin, acetylated lanolin, petrolatum, isopropyl lanolate, butyl myristate, cetyl myristate, myristyl myristate, myristyl lactate, cetyl alcohol, isostearyl alcohol and isocetyl lanolate. One or more emollients can optionally be included in the formulation.

The film formers can be in the form of film forming polymers. Non-limiting examples of film forming polymers suitable for use in formulations of the present invention include but are not limited to: from Akzo Nobel Surface Chemistry LLC, Bridgewater N.J., AMPHOMER and AMPHOMER LV-71 polymers (octylacrylamide/acrylates/butylaminoethyl methacrylate compolymer), AMPHOMER HC polymer (acrylates/octylacrylamide copolymer) BALANCE 0/55, BALANCE CR and DERMACRYL AQF polymers (acrylates copolymer), BALANCE 47 polymer (octylacrylamide/butylaminoethyl methacrylate copolymer), RESYN 28-2930 polymer (VA/crotonates/vinyl neodecanoate copolymer), RESYN 28-1310 polymer (VA/Crotonates copolymer), FLEXAN polymers (sodium polystyrene sulfonate), DynamX polymer (polyurethane-14 (and) AMP-Acrylates copolymer), RESYN XP polymer (acrylates/octylacrylamide copolymer), STRUCTURE 2001 (acrylates/steareth-20 itaconate copolymer) and STRUCTURE 3001 (acrylates/ceteth-20 itaconate copolymer); from ISP, OMNIREZ-2000 (PVM/MA half ethyl ester copolymer), GANEX P-904 (butylated PVP), GANEX V-216 (PVP/hexadecene copolymer) GANEX V-220 (PVP/eicosene copolymer), GANEX WP-660 (tricontanyl PVP), GANTREZ A425 (butyl ester of PVM/MA copolymer), GANTREZ AN-119 PVM/MA copolymer, GANTREZ ES 225 (ethyl ester of PVM/MA copolymer), GANTREZ ES425 (butyl ester of PVM/MA copolymer), GAFFIX VC-713 (vinyl caprolactam/PVP/dimethylaminoethyl methacrylate copolymer), GAFQUAT 755 (polyquaternium-11), GAFQUAT HS-100 (polyquaternium-28) AQUAFLEX XL-30 (Polyimide-1), AQUAFLEX SF-40 (PVP/Vinylcaprolactam/DMAPA Acrylates Copolymer), AQUAFLEX FX-64 (Isobutylene/Ethylmaleimide/Hydroxyethylmaleimide Copolymer), ALLIANZ LT-120 (Acrylates/C1-2 Succinates/Hydroxyacrylates Copolymer), STYLEZE CC-10 (PVP/DMAPA Acrylates Copolymer), STYLEZE 2000 (VP/Acrylates/Lauryl Methacrylate Copolymer), STYLEZE W-20 (Polyquaternium-55), Copolymer Series (PVP/Dimethylaminoethylmethacrylate Copolymer), ADVANTAGES and ADVANTAGE LCA (VinylcaprolactamNP/Dimethylaminoethyl Methacrylate Copolymer), ADVANTAGE PLUS (VA/Butyl Maleate/Isobornyl Acrylate Copolymer); from BASF, ULTRAHOLD STRONG (acrylic acid/ethyl acrylate/t-butyl acrylamide), LUVIMER 100P (t-butyl acrylate/ethyl acrylate/methacrylic acid), LUVIMER 36D (ethyl acrylate/t-butyl acrylate/methacrylic acid), LUVIQUAT HM-552 (polyquaternium-16), LUVIQUAT HOLD (polyquaternium-16), LUVISKOL K30 (PVP) LUVISKOL K90 (PVP), LUVISKOL VA 64 (PVPNA copolymer) LUVISKOL VA73W (PVPNA copolymer), LUVISKOL VA, LUVISET PUR (Polyurethane-1), LUVISET Clear (VP/MethacrylamideNinyl Imidazole Copolymer), LUVIFLEX SOFT (Acrylates Copolymer), ULTRAHOLD 8 (Acrylates/Acrylamide Copolymer), LUVISKOL Plus (Polyvinylcaprolactam), LUVIFLEX Silk (PEG/PPG-25/25 Dimethicone/Acrylates Copolymer); from Amerchol, AMERHOLD DR-25 (acrylic acid/methacrylic acid/acrylates/methacrylates); from Rohm&Haas, ACUDYNE 258 (acrylic acid/methacrylic acid/acrylates/methacrylates/hydroxyl ester acrylates from Mitsubishi and distributed by Clariant, DIAFORMER Z-301, DIAFORMER Z-SM, and DIAFORMER Z-400 (methacryloyl ethyl betaine/acrylates copolymer), ACUDYNE 180 (Acrylates/Hydroxyesters Acrylates Copolymer), ACUDYNE SCP (Ethylenecarboxyamide/AMPSA/Methacrylates Copolymer), and the ACCULYN rheological modifiers; from ONDEO Nalco, FIXOMER A-30 and FIXOMER N-28 (INCI names: methacrylic acid/sodium acrylamidomethyl propane sulfonate copolymer); from Noveon, FIXATE G-100 (AMP-Acrylates/Allyl Methacrylate Copolymer), FIXATE PLUS (Polyacrylates-X), CARBOPOL Ultrez 10 (Carbomer), CARBOPOL Ultrez 20 (Acrylates/C10-30 Alkyl Acrylates Copolymer), AVALURE AC series (Acrylates Copolymer), AVALURE UR series (Polyurethane-2, Polyurethane-4, PPG-17/IPDI/DMPA Copolymer); polyethylene glycol; water-soluble acrylics; water-soluble polyesters; polyacrylamides; polyamines; polyquaternary amines; styrene maleic anhydride (SMA) resin; polyethylene amine; and other conventional polymer that is polar solvent soluble or that can be made soluble through neutralization with the appropriate base.

The cosmetically acceptable vehicle may comprise an aqueous phase, an oil phase, an alcohol, a silicone phase or mixtures thereof. The cosmetically acceptable vehicle may also comprise an emulsion. Non-limiting examples of suitable emulsions include water-in-oil emulsions, oil-in-water emulsions, silicone-in-water emulsions, water-in-silicone emulsions, wax-in-water emulsions, water-oil-water triple emulsions or the like having the appearance of a cream, gel or microemulsions. The emulsion may include an emulsifier, such as a nonionic, anionic or amphoteric surfactant.

Personal care formulations include, without limitation, lotions, creams (including for the face and body), rinse-off body lotions, moisturizing cleansers, soaps, anti-aging products, nourishing creams and lotions, firming and toning products, shaving creams, deodorants, depilatories, color cosmetics foundations, makeups, lipsticks, sunscreens, suntan lotions, after-sun products, personal care wipes, baby care products, bath and shower products, hair shampoo, hair leave-in conditioner, hair rinse-off conditioner, hair gel, hair lotion, hair cream, mousse, hair spray, hair dyes, hair permanent wave, hair anti-frizz, and hair volumizing products.

In one embodiment, the personal care formulations of the disclosure comprise one or more thickeners, surfactants, emulsifiers, or combinations thereof. Such components can present in an amount of 0.1 or more % by weight of the personal care formulation. In some other embodiments, one or more thickeners, surfactants, emulsifiers, or combinations thereof is present from about 0.1% to about 5%, or about 0.1% to about 1%, or about 0.1% to about 0.5%, or about 0.5% to about 5%, or about 0.5% to about 1%, or about 1% to about 5%, or about 1% to about 10%, by weight of the personal care formulation.

In one embodiment, the personal care formulation of the disclosure comprises one or more thickeners and one or more emulsifiers, each present in at least 0.1 or more % by weight of the personal care formulation. In some other embodiments, each thickener and each emulsifier is independently present from about 0.1% to about 5%, or about 0.1% to about 1%, or about 0.1% to about 0.5%, or about 0.5% to about 5%, or about 0.5% to about 1%, or about 1% to about 5%, or about 1% to about 10%, by weight of the personal care formulation.

In an exemplary embodiment, the personal care formulation comprises from about 1 wt % to about 7 wt % of a compound of formula (I), about 0.5 wt % to about 7 wt % of at least one additional moisturizing compound, about 0.1 wt % to about 1 wt % of a thickener, about 0.1 wt % to about 1 wt % of an emulsifier, and about 0.1 wt % to about 1 wt % of a preservative, based on the total weight of the personal care formulation.

In another exemplary embodiment, the personal care formulation comprises from about 2 wt % to about 3 wt % of a compound of formula (I), about 2 wt % to about 3 wt % of at least one additional moisturizing compound, about 0.4 wt % to about 0.6 wt % of a thickener, about 0.4 wt % to about 0.6 wt % of an emulsifier, and about 0.4 wt % to about 0.6 wt % of a preservative, based on the total weight of the personal care formulation.

In an exemplary embodiment, the personal care formulation comprises from about 1 wt % to about 7 wt % of a compound of formula (I) and about 0.5 wt % to about 7 wt % of at least one additional moisturizing compound, based on the total weight of the personal care formulation. In another exemplary embodiment, the personal care formulation comprises from about 2 wt % to about 3 wt % of a compound of formula (I) and about 2 wt % to about 3 wt % of at least one additional moisturizing compound, based on the total weight of the personal care formulation.

In another aspect, the disclosure provides a kit comprising a container (e.g., a tube or jar) containing a formulation according to the invention and instructions for application of the formulation to the skin or hair for enhancing moisturization of the skin or hair, wherein the instructions are printed on the container, on the packaging of the container, or on a document included with the container.

In another aspect, the disclosure provides a method of moisturizing skin or hair, the method comprising applying an effective moisturizing amount of a personal care formulation of the disclosure to the skin or hair, respectively.

Definitions

The following terms and expressions used have the indicated meanings.

Throughout this specification, unless the context requires otherwise, the word “comprise” and “include” and variations (e.g., “comprises,” “comprising,” “includes,” “including”) will be understood to imply the inclusion of a stated component, feature, element, or step or group of components, features, elements or steps but not the exclusion of any other integer or step or group of integers or steps.

As used in the specification and the appended claims, the singular forms “a,” “an,” and “the” include plural referents unless the context clearly dictates otherwise.

As used herein, the term “about” refers to the given value ±10% of the value.

Ranges can be expressed herein as from “about” one particular value, and/or to “about” another particular value. When such a range is expressed, another aspect includes from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint.

All percentages, ratios and proportions herein are by weight, unless otherwise specified. A weight percent (weight %, also as wt %) of a component, unless specifically stated to the contrary, is based on the total weight of the composition in which the component is included (e.g., on the total amount of the compositions). All mol % values are based on the moles of the active compounds.

As used herein, the term “alkyl” refers to a group comprised of one to six, unless otherwise noted, saturated carbon atoms connected in a linear or branched configuration. Examples of linear alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl. Examples of branched alkyl groups include iso-propyl (1-methylethyl), tert-butyl (1,1-dimethylethyl), iso-butyl (2-methylpropyl), sec-butyl (1-methylpropyl), iso-pentyl (2-methylbutyl), neopentyl (2,2-dimethylpropyl), iso-hexyl (2-methylpentyl, 3-methylpentyl, and 2,3-dimethylbutyl), and neohexyl (2,2-dimethylbutyl).

As used herein, the term “cosmetically acceptable” means suitable for use in contact with the skin or hair of most humans and most members of lower animal species without undue toxicity, incompatibility, instability, irritation, allergic response, and the like.

EXAMPLES

The methods of the disclosure are illustrated further by the following examples, which are not to be construed as limiting the disclosure in scope or spirit to the specific procedures and in them.

Example 1 Preparation of Diglycolamine (DGA) Acetamide/Glycerol Blend

A mixture of 94.63 g (0.9 mol) 2-(2-aminoethoxy)ethanol, 65.46 g (0.3 mol) of 1,2,3-triacetoxypropane (triacetin), and 1.24 g potassium carbonate was stirred and heated at about 120-125° C. in a 250 ml round bottom flask immersed in an oil bath under N₂ atmosphere. The mixture was stirred until the reaction showed complete conversion of triacetin to the product as monitored by IR for disappearance of ester carbonyl peak in triacetin at 1739 cm⁻¹ and appearance of amide carbonyl peak for the product at 1646 cm⁻¹ wavenumber, both as monitored by FTIR (using a single-bounce ATR accessory with ZnSe crystal and DTGS detector with a Nicolet iS10 spectrometer). The liquid product (161.33 g) thus obtained is a mixture of DGA Acetamide and glycerol in 3:1 molar ratio, which corresponds to 83 wt % DGA Acetamide and 17 wt % glycerol.

Example 2 Preparation of Diglycolamine (DGA) Acetamide

A mixture of 42.06 g (0.4 mol) of 2-(2-aminoethoxy)ethanol, 70.49 g (0.8 mol) of ethyl acetate, and 0.33 g of phosphorous acid was refluxed in a 250 ml round bottom flask immersed in an oil bath under N₂ atmosphere. The mixture was refluxed until the reaction showed no further increase in the ratio of amide carbonyl peak (due to product) at 1646 cm⁻¹ wavenumber as monitored by FTIR (using a single-bounce ATR accessory with ZnSe crystal and DTGS detector with a Nicolet iS10 spectrometer). The excess ethyl acetate and the ethanol byproduct were then distilled off through downward distillation. Fresh ethyl acetate (35.24 g, 0.4 mol) was then added to the reaction mixture and the refluxing was continued until no further increase in the product formation was seen in the amide carbonyl peak at 1646 cm⁻¹ as monitored by FTIR. This process of stripping of excess ethyl acetate/ethanol and adding fresh ethyl acetate was repeated until the FTIR showed it to be the desired product no further increase in the amide carbonyl peak at 1646 cm⁻¹, indicating that the reaction of 2-(2-aminoethoxy)ethanol had gone to completion.

Example 3 Dynamic Vapor Sorption Analysis

Dynamic Vapor Sorption (DVS) technique was used to measure the moisture intake of a specific compound at certain humidity level. DVS Intrinsic instrument manufactured by Surface Measurement Systems UK Ltd. (London, United Kingdom) was used to measure DVS. The following measurement procedure was used to determine the water vapor absorption of a specific composition.

A uniform aqueous solution of a target composition was made at 50% concentration. About 1.2 to 1.6 mg of the prepared aqueous solution was added to DVS instrument at zero tare balance. The temperature was then set at 25° C. A measurement was performed at 90% humidity to ensure that the sample absorbs the highest level of water in order to minimize the mass transfer barrier during the evaporation process. The dynamics of water absorption was determined by the weight change per minute; with water absorption equilibrium defined as the time at which the weight change per minute was less than 0.005% of the sample weight. The equilibrium weight at 0% humidity is the sample weight by itself. Thus, the percentage of equilibrium water absorption at various humidity levels was calculated.

Using the above procedure, DVS was used to evaluate water absorption for compositions comprising DGA Acetamide, other moisturizing agents, and combinations of DGA Acetamide and various additional moisturizing agents. First, DVS values were obtained at 50% humidity for the DGA acetamide products of Examples 1 and 2 above and other selected moisturizing agents. The results are shown in Table 1.

TABLE 1 Dynamic Vapor Sorption (DVS) Values of Moisturizing Agents % water absorbed (based on Sample Moisturizing Agent weight of moisturizing agent) A Hydroxyethyl urea 19.7 B DGA Acetamide:glycerol 22.3 (83 wt %:17 wt %, Ex. 1) C DGA Acetamide (Ex. 2) 26.9 D Glycerol 27.7 E Sodium PCA 28.7 F Sodium lactate 35.1 Then, 1:1 mixtures based on weight were made of each of the DGA Acetamide products of Examples 1 and 2 above with each of the other four moisturizing agents, where the DGA acetamide product of Example 1 is DGA Acetamide:glycerol (83 wt %:17 wt %) and the DGA acetamide product of Example 2 is substantially 100% DGA acetamide. DVS measurements were taken at 50% humidity, using the same amount of total moisturizing agent. It was expected that the DVS values of the mixtures with the other four moisturizing agents would have been the average of the DVS values of each of the moisturizing agents individually, based on the weight percent of each in the mixture. Instead, in almost all cases it was found that the DVS values of the mixtures with the other four moisturizing agents were greater than the average of the two moisturizing agents individually, as shown in Table 2, with the typical standard deviation of measure being ±0.1%.

TABLE 2 DVS Values of Mixtures of Moisturizing Agents, Calculated and Measured Measured % Moisturizing agent Calculated % water water Sample combination (1:1) absorbed absorbed G Hydroxyethyl urea:DGA (19.7 + 22.3)/2 = 21 24.5 Acetamide/Glycerol (Ex. 1) H Hydroxyethyl urea:DGA (19.7 + 26.9)/2 = 23.3 24.8 Acetamide (Ex. 2) I Glycerol:DGA (27.7 + 22.3)/2 = 25 31.4 Acetamide/Glycerol (Ex. 1) J Glycerol:DGA Acetamide (27.7 + 26.9)/2 = 27.3 27.0 (Ex. 2) K Sodium lactate:DGA (35.1 + 22.3)/2 = 28.7 42.3 Acetamide/Glycerol (Ex. 1) L Sodium lactate:DGA (35.1 + 26.9)/2 = 31 47.1 Acetamide (Ex. 2) M Sodium PCA:DGA (28.7 + 22.3)/2 = 25.5 42.7 Acetamide/Glycerol (Ex. 1) N Sodium PCA:DGA (28.7 + 26.9)/2 = 27.8 44.2 Acetamide (Ex. 2) The measured values of % water absorbed as presented in Tables 1 and 2 are illustrated in FIG. 4. The data show that mixtures of each of the DGA acetamide products of Examples 1 and 2 with each of the other moisturizing agents performed better than the calculated DVS values based on the DVS values of each moisturizing agent alone. This was true regardless of whether the DGA Acetamide used was the 83:17 wt % mixture with glycerol, as prepared by the process of Example 1, or the pure DGA acetamide, as prepared by the process of Example 2 (except for the sample of a 1:1 blend of Glycerol:DGA Acetamide of Ex. 2 , in which the calculated value was slightly higher than the measured value).

Example 4 Corneometer Analysis Gel Formulation

To prepare a gel formulation, deionized water was added to a 4 oz. tall jar that was set up for mixing using an overhead mixer and a jiffy blade. The water was then mixed at a speed that created a good vortex that nearly reached the bottom of the jar (e.g., about 700 rpm). To this, Carbopol® 940 (cross-linked polyacrylate polymer available from Lubrizol, Wickliffe, Ohio) was slowly added and mixed for at least 15 minutes until homogeneous. Triethanolamine (TEA) was then added and the mixing speed was adjusted overhead to about 200 rpm and continued mixing for about 10 minutes (e.g., product viscosity increased). To this mixture was added 5 wt % of the moisturizing agent, as either a single agent or a combination of agents, followed by 0.5 wt % Glydant™ Plus™ (a preservative available from Lonza, Basel, Switzerland) and the remaining, balance water. Mixing was continued at 200 rpm for about 15-20 minutes. The mixture was then removed from the mixer and the final pH was measured. Prior to analysis, samples were centrifuged at 2000 rpm for 15 minutes to remove suspended air pockets from the gel formulation. The final test gel formulation concentrations are provided in Table 3.

TABLE 3 Corneometer test gel formulations Ingredients Amount (wt %) deionized water 93.5  moisturizing agent(s) 5.0 (total active) Glydant ™ Plus ™ Liquid 0.5 Carbopol ® 940 0.5 TEA 0.5

Corneometer Measurement

About 30 μl of each test gel formulation was applied once (e.g., in a single application with no additional re-applications) in a circle with diameter of about 3 cm on the inner forearm of each panelist. Moisture levels were measured using a Corneometer® CM 825 (available from CK Industries) prior to application of the test gel formulations, and at 6 hour and 30 hour intervals after application, at a temperature of 22° C. and relative humidity of 50%.

Results

FIG. 2 shows the corneometer readings for eight panelists for two gel test formulations in which the active ingredients were glycerol and water, respectively, taken 6 hours after application of the gels. The actual readings for both water and glycerol for each of the 8 panelists were different, indicating individual variations in response to the gel test formulations, and differences in inherent moisture levels for each panelist. As a result of these individual differences, the average of corneometer readings over 8 panelists gave a large standard deviation.

To facilitate more meaningful comparisons of the corneometer data for the different test formulations, the following adjustment were made to minimize the variations in the response of humectant treatment: the moisturization performance for glycerol was defined to be 1, and that for water to be zero, then the scaled moisturization performance (SMP) for a specific moisturizing active was defined as:

${SMP} = \frac{R_{Active} - R_{water}}{R_{glycerol} - R_{water}}$

R_(Active), R_(water), and R_(glycerol) were the actual corneometer readings of the test gel formulations comprising the active moisturizing agent(s), water, and glycerol, respectively, for an individual panelist at a specific time after the initial treatment. The overall SMP of each tested activewas then the average of SMP over 8 panelists. FIG. 3 shows the actual corneometer readings for test gel formulations in which the moisturizing agent active was DGA Acetamide made by the process of Example 1 for 8 panelists over 6 hours, and FIG. 4 shows the scaled SMP values. The SMP values illustrated in FIG. 4 provide narrower standard deviations over 8 panelists when compared to actual corneometer readings in FIG. 3.

Using this procedure, corneometer measurements were taken at 6 hours and 30 hours for hydroxyethyl urea, glycerol, the DGA acetamide:glycerol (83:17 wt %) of Example 1, the DGA Acetamide of Example 2, a 1:1 mixture of the DGA Acetamide of Example 2 with hydroxyethyl urea, and a 1:1 mixture of the DGA Acetmaide of Example 2 with glycerol. Measurements were taken at six hours and 30 hours on eight subjects, and calculated as scaled moisturization performance values. The averages of the eight scaled values for each gel test formulation evaluated are shown in Table 4.

TABLE 4 Scaled Corneometer results at 6 and 30 hours Corneometer SMP results Active 6 hours 30 hours DGA Acetamide (Ex. 2) 0.80 0.92 DGA acetamide + Glycerol (Ex. 1, 0.88 1.36 83:17) Hydroxyethyl urea 0.91 1.03 Glycerol 1.0 1.0 DGA Acetamide (Ex. 2) + 1.02 1.18 hydroxyethyl urea DGA Acetamide (Ex. 2) and 1.09 1.24 glycerol The scaled corneometer results of the test formulations with actives that are combinations of moisturizing agents show that the measured values are greater than the calculated values based on the Corneometer readings of the moisturizing agents taken individually, as shown in Table 5, and illustrated in FIGS. 5 and 6.

TABLE 5 Comparison of calculated and measured scaled Corneometer values at 6 hours and 30 hours Corneometer results 6 hours 30 hours Moisturizing actives calculated measured calculated measured DGA Acetamide + (0.80 ) (0.83) + 0.88 (0.92) (0.83) + 1.36 Glycerol (Ex. 1; 1.0 (0.17) = 1.0 (0.17) = 83:17) 0.83 0.93 DGA Acetamide (Ex. (0.80 + 1.02 (0.92 + 1.03)/2 = 1.18 2) + hydroxyetheyl 0.91)/2 = 0.85 0.98 urea (1:1) DGA Acetamide (Ex. (0.80 + 1.0)/2 = 1.09 (0.92 + 1.0)/2 = 1.24 2) + Glycerol (1:1) 0.9 0.96

The data in table 5 demonstrates that the measured scaled corneometer readings for moisturizing actives containing DGA acetamide and either glycerol of hydroxyethyl urea are higher than the values that would have been predicted by calculation based on the SMP values of each agent measured individually, both at six hours and at 30 hours.

It is understood that the examples and embodiments described herein are for illustrative purposes only and that various modifications or changes in light thereof will be suggested to persons skilled in the art and are to be incorporated within the spirit and purview of this application and scope of the appended claims. All publications, patents, and patent applications cited herein are hereby incorporated herein by reference for all purposes. 

1. A personal care formulation comprising (a) a moisturizing agent of formula (I)

wherein n is an integer from 2 to 5; R¹ is independently H or C₁-C₃ alkyl; and R² is an unsubstituted linear or branched C₁-C₄ alkyl; and (b) at least one additional moisturizing agent; and (c) a cosmetically acceptable vehicle.
 2. The personal care formulation of claim 1, wherein the at least one additional moisturizing agent of component (b) is selected from petrolatum, mineral and vegetable oils, lanolins, glycerol, sorbitol, polyols, urea, hydroxyalkylurea, lactic acid, lactates, sugars, alpha hydroxy acids, beta hydroxy acids, sodium hyaluronate, hyaluronic acid, pyrrolidone carboxylic acid, and pyrrolidone carboxylates, or a combination thereof.
 3. The personal care formulation of claim 1, wherein the at least one additional moisturizing agent of component (b) is selected from glycerol, polyols, hydroxyalkyl ureas, pyrrolidone carboxylic acids and salts thereof, lactic acids and salts thereof, or a combination thereof.
 4. The personal care formulation of claim 3, wherein the weight ratio of the moisturizing agent of formula (I) of component (a) to the at least one additional moisturizing agent of component (b) is from about 10:1 to about 1:10, or from about 5:1 to about 1:5 about 3:5, or about 3:4, or about 1:1.2 to about 1:1.3 by weight.
 5. The personal care formulation of claim 1, wherein n is
 2. 6. The personal care formulation of claim 1, wherein R² is methyl.
 7. The personal care formulation of claim 1, wherein R¹ is H.
 8. The personal care formulation of claim 1, wherein the moisturizing agent of formula (I) is:


9. The personal care formulation of claim 1, wherein the moisturizing agent of formula (I) is present in about 0.5% to about 15% by weight of the personal care formulation.
 10. The personal care formulation of claim 1, wherein the at least one additional moisturizing agent of component (b) is present in about 0.5% to about 15% by weight of the personal care formulation.
 11. The personal care formulation of claim 1, further comprising one or more additives selected from the group consisting of a thickener, suspending agent, emulsifier, pH adjuster, humectant, moisturizer, emollient, oil, wax, solvent, chelating agent, vitamin, antioxidant, botanical extract, silicone, neutralizing agent, preservative, fragrance, dye, pigment, conditioner, polymer, antiperspirant active ingredient, anti-acne agent, anti-dandruff active, surfactant, exfoliant, film former, propellant, UV filter, sunscreen active, tanning accelerator, hair fixatives and colorant, and combinations thereof.
 12. The personal care formulation of claim 1, for use as a skin care composition or a hair care composition.
 13. The personal care formulation of claim 1, wherein the formulation is selected from the group consisting of lotions, creams, rinse-off body lotions, moisturizing cleansers, soaps, anti-aging products, nourishing creams and lotions, firming and toning products, shaving creams, depilatories, deodorants, color cosmetics foundations, makeups, lipsticks, sunscreens, suntan lotions, after-sun products, personal care wipes, baby care products, and bath and shower products, shampoo, leave-in conditioner, rinse-off conditioner, hair gel, hair lotion, hair cream, mousse, and hair spray.
 14. A method of moisturizing skin or hair in a subject, the method comprising applying an effective moisturizing amount of a personal care formulation of claim 1 to the skin or hair of the subject.
 15. (canceled) 